A Dihydrodinaphthoheptacene

Romain, Maxime; Quinton, Cassandre; Roisnel, Thierry; Jacques, Emmanuel; Rault‐Berthelot, Joëlle; Poriel, Cyril

doi:10.1021/acs.joc.7b02834

Cited by 9 publications

(3 citation statements)

References 42 publications

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“…Regarding the redox properties (Table ), in the whole series, benzoheterocycle-fused pyrenes are easier to oxidize and reduce compared to pyrene measured in the same conditions, thus confirming the lower gap measured by optical method, in particular in case of 3 and 5 . Furthermore, P = O-containing pyrenes display reversible reduction at relatively low potential (Table ).…”

Section: Resultssupporting

confidence: 69%

Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene

et al. 2018

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Section: Resultssupporting

confidence: 69%

Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene

et al. 2018

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“…It reveals that the absorption spectra nearby 222−298 nm which may be ascribed due to the π−π* transitions of benzilimidazole and phenyl rings. 39,40 However, well-built absorption spectra at around 360−363 nm may be ascribed due to the transitions of π−π* as well as intramolecular charge transfer (ICT) among benzilimidazole and TPA. 41 The emission spectra of the fluorophores in solution (Figure 7b) demonstrate the peaking wavelength around 430, 431, and 436 nm for PHBI-fl-TPA, PTBI-fl-TPA, and MCFBI-fl-TPA, respectively.…”

Section: ■ Synthesismentioning

confidence: 99%

Solution Processable Deep-Blue OLEDs Based on Benzimidazole-TPA Conjugated through 9,9-Diethyl Fluorene (D-π-A) Luminophore with a Hybridized Local and Charge Transfer Excited State

et al. 2023

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Blue emitters with outstanding luminous performance must be synthesized for full-color organic light-emitting diode displays. The hybridized local and charge transfer (HLCT) is a remarkable excited state that combines the local and CT state to ensure a significant fluorescence quantum yield. The ambition of this study is to implement a subtle interpretation of photophysical and electroluminescence (EL) properties. To understand more about the geometry and orientations, the density functional theories were studied. Herein, we present a hybrid donor-π-acceptor blue-emitting fluorophore with a twisted geometry, in which triphenylamine (TPA) acts as a donor, 9,9 diethylfluorene acts as a spacer, and benzilimidazole acts as an acceptor. The EL spectra of the device are very similar to spectra of photoluminescence in the solution phase. Among all, the best performing 15 wt % MCFBI-fl-TPA-based OLED device illustrates a maximum luminance of 3290 cd/m 2 . The device shows 8.2 lm W −1 of power efficiency, 7.9 cd A −1 of current efficiency, and 3.5% of high external quantum efficiency with (0.20, 0.23) of CIE coordinates of the device emitting blue color.

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“…Even though organics-based ultraviolet materials possess these advantages, obtaining high-performance ultraviolet organic materials still faces lots of obstacles. The traditional deep-blue fluorophores, such as anthracene [ 13 ], aromatic hydrocarbons [ 14 ], dihydrodinaphthoheptacene [ 15 ], carbazole [ 16 ], fluorene [ 17 ], triphenylamine [ 18 ], phenylene [ 19 ], pyrene [ 20 ] and phosphorescent iridium complexes [ 21 ] showed good performance in dilute solution, but urgent demands for further improvements remain regarding ultraviolet color purity, intermolecular stacking, solid-state morphology, efficiency and device lifetime. For instance, the negative aggregation of molecules in the solid state could induce red-shifted emissions and aggregation quench, the consequences limit the realization of pure ultraviolet emission.…”

Section: Introductionmentioning

confidence: 99%

π-Bridge Effect on Symmetric Carbazole-Based Small Molecules for Realizing Ultraviolet Fluorescent Emission

et al. 2018

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A series of symmetric carbazole derivatives (CzP-H, CzP-CN, CzP-Me, and CzP-OMe), which comprise electron-donating and electron-drawing groups appending on a phenyl core, was synthesized and characterized in detail. These compounds exhibit excellent thermal stabilities, with thermal decomposition temperatures exceeding 400 °C. From the fluorescent spectra in film, CzP-H, CzP-Me, and CzP-OMe showed UV to blue-violet emission, with peaks at 396 nm, 402 nm, and 392 nm, respectively. The E00 energies of CzP-H, CzP-CN, CzP-Me, and CzP-OMe were 3.39 eV, 2.83 eV, 3.50 eV, and 3.35 eV, respectively. From the electrochemical measurements, the highest occupied molecular orbital (HOMOs) energy levels were −5.30 eV, −5.64 eV, −5.46 eV, and −5.24 eV for CzP-H, CzP-CN, CzP-Me, and CzP-OMe, respectively. Through calculations from HOMO energy levels and E00 energies, the lowest unoccupied molecular orbital (LUMOs) energy levels of CzP-H, CzP-CN, CzP-Me, and CzP-OMe were −1.91 eV, −2.81 eV, −1.96 eV, and −1.89 eV, respectively. Therefore, the introduction of different substitutes in phenyl cores would distinctly affect the photophysical properties. These results indicate that the prepared carbazole derivatives could be potential candidates for realizing ultraviolet or blue-violet emission.

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A Dihydrodinaphthoheptacene

Abstract: We report the first example of a dihydrodinaphthoheptacene derivative and the mechanistic investigations of the regioselective electrophilic intramolecular cyclization reaction involved in the synthesis. The structural, electrochemical, and photophysical properties have been investigated.

Cited by 9 publications

References 42 publications

Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene

Synthesis, Optical, and Redox Properties of Regioisomeric Benzoheterocycles-Fused Pyrene

Solution Processable Deep-Blue OLEDs Based on Benzimidazole-TPA Conjugated through 9,9-Diethyl Fluorene (D-π-A) Luminophore with a Hybridized Local and Charge Transfer Excited State

π-Bridge Effect on Symmetric Carbazole-Based Small Molecules for Realizing Ultraviolet Fluorescent Emission

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